Boston’s front office chief has already been to the NBA’s mountaintop; first as player winning a pair of championships in the 80s and then as the architect of the Big 3 that brought the Celtics their 17th NBA championship in 2008.

He’s since progressed from Kevin Garnett’s triumphant “Anything’s possible” declaration in ’08, to believing in the possibilities of the present with a corps of young talent that’s two wins away from returning the franchise to the conference finals for the first time since 2012.

But with the East’s top seed locked in 2-2 tie with Washington, the outcome of this series could go a long way toward affirming the recent moves Ainge has made, or exposing the holes that still exist as his team chases banner No. 18.

“Make no mistake that we did try to improve our team,” Ainge said. “But we do have a lot of confidence in our team and the guys that don’t get a chance to play. It doesn’t seem really fair when we have guys that are healthy and that we like and aren’t even getting on the court to bring in other guys just because they’re playing and everyone assumes they’re better.”

After brushing off initial overtures, Ainge was lured back to Boston as the president of basketball operations in 2003 with the endorsement of none other than Celtics’ legend Red Auerbach.

The way Ainge once told the story to a church group, Auerbach called Ainge “the luckiest guy I know” in recommending him to owners Wyc Grousbeck and Steve Pagliuca.

While Ainge has acknowledged some fortunate outcomes to get the Celtics back to this point, such as the rise of Isaiah Thomas into an All-Star, there have also been plenty of pivotal moves by Ainge.

One of the league’s most-tenured front office heads, he has recently used that experience to his advantage.

It started with the hiring of Stevens, then just a 37-year-old college coach at Butler, in 2013. That was followed by the trade of Garnett and Paul Pierce to Brooklyn, which netted the Celtics three first-round picks and the right to swap picks with the Nets this season.

That led to the drafting of rookie Jaylen Brown last summer and a wealth of possibilities with this year’s Brooklyn pick, which has the best odds of being No. 1 overall.

It’s a bargaining chip that only still exists because of Ainge’s decision to not make any trade deadline in each of the last two years.

Though Boston did miss on wooing Kevin Durant to town last summer, it was able to land big man Al Horford, who has since credited Ainge’s vision as one of the major factors that swayed him to sign.

Horford’s addition has not only has provided the Celtics with needed veteran leadership, but he’s been one of the sustaining elements for a group that was able to rally behind Thomas after his sister’s sudden passing on the eve of the playoffs.

“I think that that showed the character of all the players involved,” Ainge said. “I think the first two games (of Chicago series) there was a little bit of a cloud because one of our family was hurting really, really bad…It was like no one knew how to really react to the whole situation. Credit goes to Isaiah, first and foremost, for inspiring his team and the team for fighting for Isaiah.”

TNT analyst and former NBA coach Kevin McHale played alongside Ainge as a player and later saw him in action as an executive. He said while the word patient didn’t used to be one he’d have used to describe his friend, it is one example of how his style has evolved.

McHale said Ainge has also shown a willingness to bring tools like analytics into how he looks at his roster — even if at the end of the day he ultimately still relies on his instincts.

“He’s not a pigeonhole guy,” McHale said. “He uses everything and I think you have to…He has a good eye for grit and toughness. None of that analytics can show that.”

Whether it’s luck or skill, Ainge isn’t waiting for an 18th banner to fall in his lap.

“It’s like being player…You don’t sit around and wait for luck,” Ainge said. “You work your way into having good fortune go your way. You behave and act certain way with integrity and character so that when opportunities present themselves you’re ready.”

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